Citation: Zhen Tang DONG, Zu Wang WU, Zhi Wei WANG, Yun De WANG, Yin Zhou YU. A Study on Side Reactions of Hydroxyethylation of 3-Nitro-4-chlorobenzenesulfinic Acid with Ethylene Oxide[J]. Chinese Chemical Letters, ;2006, 17(5): 613-616. shu

A Study on Side Reactions of Hydroxyethylation of 3-Nitro-4-chlorobenzenesulfinic Acid with Ethylene Oxide

1.
The State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012;
2.
Dankong Industrial and Trade Co. Ltd., Taizhou 318000

Received Date: 21 October 2005

The reaction of 3-nitro-4-chlorobenzenesulfinic acid and ethylene oxide to obtain 2-nitro-4-(β-hydroxyethylsulfonyl)chlorobenzene had been studied. Except hydroxyethylation on the sulfur atom of 3-nitro-4-chlorobenzenesulfinic acid to form the target product, 2-nitro-4-(β-hydroxyethylsulfonyl)chlorobenzene, there presented three kinds of side reactions: 1. Condensation and elimination of HCl to form biphenyl sulfone derivatives; 2. Addition to give bisulfonyl ethane derivative via vinyl sulfone; and 3. Hydroxylethylation on O-atom to produce hydroxylethylsulfinate due to the tautomerism of sulfinic acid.
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